N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(pyridine-2-sulfonyl)-tetrahydro-pyran-3-yl]-acetamide

Base Information

Chemical Name:N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(pyridine-2-sulfonyl)-tetrahydro-pyran-3-yl]-acetamide
CAS No.:203716-55-6
Molecular Formula:C₃₄H₃₆N₂O₇S
Molecular Weight:616.735
Hs Code.:

Synonyms:N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(pyridine-2-sulfonyl)-tetrahydro-pyran-3-yl]-acetamide

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Chemical Property of N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(pyridine-2-sulfonyl)-tetrahydro-pyran-3-yl]-acetamide

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Technology Process of N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(pyridine-2-sulfonyl)-tetrahydro-pyran-3-yl]-acetamide

There total 8 articles about N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(pyridine-2-sulfonyl)-tetrahydro-pyran-3-yl]-acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 12.0%

: 203716-54-5
N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(pyridin-2-ylsulfanyl)-tetrahydro-pyran-3-yl]-acetamide

: 4171-72-6,4171-79-3,121123-45-3
2-acetamido-2-deoxy-3,4,6-tri-O-benzyl-D-galactopyranose

: 203716-55-6
N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(pyridine-2-sulfonyl)-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 2.5h;
DOI:10.1021/jo971727h

Reference yield:

: 79781-69-4
2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose

: 203716-55-6
N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(pyridine-2-sulfonyl)-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1 h / 30 °C

2: 99 percent / trimethylsilyl triflate, molecular sieves 4A / CH₂Cl₂ / 1 h / -20 °C / other reagent: BF₃*Et₂O

3: SnCl₂, thiophenol, triethylamine / acetonitrile / 0.33 h / 20 °C / other reagents: triphenylphosphine, NiCl₂/NaBH₄, SmI₂

4: 89 mg / pyridine

5: 12 percent / m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 2.5 h / 0 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydrogencarbonate; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; tin(ll) chloride; In dichloromethane; acetonitrile;
DOI:10.1021/jo971727h

Reference yield:

: 2637-34-5,73018-10-7
2-Sulfanylpyridine

: 203716-55-6
N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(pyridine-2-sulfonyl)-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:: Multi-step reaction with 4 steps

1: 0.62 g / BF₃*Et₂O / CH₂Cl₂ / 1 h / -15 °C / other reagent: trimethylsilyl triflate

2: SnCl₂, thiophenol, triethylamine / acetonitrile / 0.33 h / 20 °C / other reagents: triphenylphosphine, NiCl₂/NaBH₄, SmI₂

3: 89 mg / pyridine

4: 12 percent / m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 2.5 h / 0 °C

With pyridine; boron trifluoride diethyl etherate; sodium hydrogencarbonate; thiophenol; triethylamine; 3-chloro-benzenecarboperoxoic acid; tin(ll) chloride; In dichloromethane; acetonitrile;
DOI:10.1021/jo971727h